sintesis makromolekul kaliks[4]resorsinarena...
TRANSCRIPT
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SINTESIS MAKROMOLEKUL KALIKS[4]RESORSINARENA
ALKILAMINO DAN PERBANDINGAN KAPASITAS EKSTRAKSINYA TERHADAP LOGAM Pb(II)
Oleh:
Ratnaningsih E. Sardjono, Jumina, Hardjono Sastrohamidjojo, Sri Juari Santosa
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LATAR BELAKANG
KANDUNGAN SIGNIFIKAN
LOGAM BERAT Pb(II) DI
PERAIRAN BERBAHAYA BAGI
LINGKUNGAN PERLU TEKNOLOGI
UNTUK MENGURANGI KANDUNGAN
LOGAM BERAT: EKSTRAKSI
TETRAMER SIKLIK KALIKSARENA BERPOTENSI
SEBAGAI ADSORBEN
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KALIKSARENA
MEMPUNYAI GEOMETRI MOLEKUL UNIK,
BERBENTUK KERANJANG
DAN BERONGGA.
DAPAT DIMODIFIKASI SECARA LUAS
TELAH DIGUNAKAN
UNTUK BERBAGAI
KEPERLUAN: EKSTRAKSI
(Sonoda dkk,1999),
SENSOR (Mc Mahon
dkk,2001), MEMBRAN (Lin
dkk,2005), SURFAKTAN
dan KATALIS
(Shinkai,1986), FASA DIAM
KHROMATOGRAFI (Suh dkk,2001)
KALIKSARENA ADALAH OLIGOMER SIKLIS YANG
TERSUSUN DARI SATUAN-SATUAN AROMATIS YANG
DIHUBUNGKAN OLEH SUATU JEMBATAN.
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SKEMA SINTESIS
resorsinol
OHHO
CH3CH
O
+
asetaldehida
HCl, CH 3CH2OH
15oC 30 menit,
50oC 1 jam,
25oC 4 hari
(CH3)2NH, HCHO
temp. kamar 20 jam
OHHO
OH
OH
OHHO
HO
HO
N
N
N
N
HO
HO
HO OH
OH
OH
HO OH
C-metilkaliks[4]resorsinarena
Tetrakis(dimetilamino)metilC-metilkaliks[4]resorsinarena
N
N
N
N
HO
HO
HO OH
OH
OH
HO OH
Tetrakis(dietilamino)metilC-metilkaliks[4]resorsinarena
O
N
O
N
O
N
O
N
HO
OH
OH
HO
CH3CH2CH2NH2,
HCHO70oC, 14 jam
30oC, 28 jam
(CH3CH2)2NH,
HCHO
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SINTESIS C-METILKALIKS[4]RESORSINARENA
resorsinol
OHHO
CH3CH
O
+
asetaldehida
HCl, CH 3CH2OH
15oC 30 menit,
50oC 1 jam,
25oC 4 hari
Spektrum IR
OHHO
OH
OH
OHHO
HO
HO
C-metil kaliks[4]resorsinarenapadatan putih
t.l > 390oC
70-85%
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Spektrum MS C-MetilKaliks[4]resorsinarena
M+
M+-CH3
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Spektrum 13C NMR C-Metil Kaliksresorsinarena
OH
OH
OHHO
HO
HO
HOOH
131.1
123.3
156.1
103.9
156.1
123.3
131.1
123.3
156.1
103.9
156.1
123.3
131.1
123.3 156.1
103.9
156.1123.3
131.1
123.3156.1
103.9
156.1123.3
18.6 18.6
18.618.6
24.9
24.924.9
24.9
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Spektrum 1H NMR C-MetilKaliks[4]resorsinarena
OH
OH
OHHO
HO
HO
HOOH
7.22
6.86
7.22
6.86
7.22 6.867.226.86
4.23 4.23
4.234.23
1.62
1.621.62
1.62
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SINTESIS TETRAKIS(DIMETILAMINO)METIL C-METILKALIKS[4]RESORSINARENA (TDEACMKR)
(CH3)2NH, HCHO
temp. kamar 20 jam
OHHO
OH
OH
OHHO
HO
HO
N
N
N
N
HO
HO
HO OH
OH
OH
HO OH
C-metilkaliks[4]resorsinarena
Tetrakis(dimetilamino)metilC-metilkaliks[4]resorsinarena
Padatan putih kemerahan
35,26%
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SPEKTRUM IR TETRAKIS(DIMETILAMINO)METIL
C-METILKALIKS[4]RESORSINARENA
HO
HO
HO OH
OH
OH
HO OH
N
N
N
N
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HO
HO
HO OH
OH
OH
HO OH
N
N
N
N
01234567PPM
Spektrum HNMR Tetrakis (Dimetilamino)metil C-metilkaliks[4]arena
F
E
D
CB
A
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SINTESIS TETRAKIS (DIETILAMIN)METIL C-METIL
KALIKS[4]RESORSINARENA
(Et)2NH, HCHO
temp. kamar 28 jam
OHHO
OH
OH
OHHO
HO
HO
N
N
N
N
HO
HO
HO OH
OH
OH
HO OH
C-metilkaliks[4]resorsinarena
Tetrakis(dietilamino)metilC-metilkaliks[4]resorsinarena
Padatan putih kemerahan
88,23%
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SPEKTRUM IR TETRAKIS (DIETILAMIN)METIL C-METIL
KALIKS[4]RESORSINARENA
N
N
N
N
HO
HO
HO OH
OH
OH
HO OH
Tetrakis(dietilamino)metilC-metilkaliks[4]resorsinarena
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N
N
N
N
HO
HO
HO OH
OH
OH
HO OH
0246PPM
Spektrum H NMR Tetrakis (Dietilamin)metil C-metil Kaliks[4]resorsinarena
A B
C
DF
E
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SINTESIS N-PROPIL DIHIDROOXAZINA C-METIL KALIKS[4]RESORSINARENA
CH3(CH2)2NH2, HCHO
70 oC, 14 jam
OHHO
OH
OH
OHHO
HO
HO O
N
O
N
O
N
O
N
HO
OH
OH
HO
C-metilkaliks[4]resorsinarena
N-Propil Dihidrooxazina C-metilkaliks[4]resorsinarena
Padatan putih kekuningan
42,46%
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SPEKTRUM IR N-PROPIL DIHIDROOXAZINA C-METIL KALIKS[4]RESORSINARENA
O
N
O
N
O
N
O
N
HO
OH
OH
HO
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SPEKTRUM HNMR N-PROPIL DIHIDROOXAZINA C-METIL KALIKS[4]RESORSINARENA
HO
OH
OH
HO
O
N
O
N
O
N
O
N7.09
4.23
7.09
4.23
7.09
4.23 7.094.23
1.621.62
1.621.62
5.013.62
5.01
3.62
5.01 3.62
5.01
3.622.36
1.43
0.96
2.36
1.43
0.96
2.36
1.43
0.96
2.36
1.43
0.96
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KAPASITAS EKSTRAKSI
0
10
20
30
40
50
60
70
80
90
100
3 3.5 4.5 5 5.5
pH
Persen
Terekstr
aksi
(%)
TDEACMKR
NPOCMKR
TDMCMKR
URUTAN KAPASITAS ADSORPSI:
NPOCMKR(93%) > TDMCMKR
(83%)>TDEACMKR (79%)